PT99038A - Processo para a preparacao de novos derivados heterociclicos do imidazol e de composicoes farmaceuticas que os contem - Google Patents

Info

Publication number

PT99038A

PT99038A PT99038A PT9903891A PT99038A PT 99038 A PT99038 A PT 99038A PT 99038 A PT99038 A PT 99038A PT 9903891 A PT9903891 A PT 9903891A PT 99038 A PT99038 A PT 99038A

Authority

PT

Portugal

Prior art keywords

methyl

imidazo

pyridine

nmr

pyrrolyl

Prior art date

1990-09-25

Links

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• 238000002360 preparation method Methods 0.000 title claims abstract description 249
• 238000000034 method Methods 0.000 title claims abstract description 145
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 182
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 95
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
• 239000001257 hydrogen Substances 0.000 claims abstract description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 21
• 230000008569 process Effects 0.000 claims abstract description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
• 125000001424 substituent group Chemical group 0.000 claims abstract description 13
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 11
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
• 150000002367 halogens Chemical class 0.000 claims abstract description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
• -1 imidazolyl imidazolyl group Chemical group 0.000 claims description 189
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 84
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 58
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 42
• 238000006243 chemical reaction Methods 0.000 claims description 39
• 125000005843 halogen group Chemical group 0.000 claims description 37
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 102000005862 Angiotensin II Human genes 0.000 claims description 13
• 101800000733 Angiotensin-2 Proteins 0.000 claims description 13
• CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims description 13
• 229950006323 angiotensin ii Drugs 0.000 claims description 13
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 239000007858 starting material Substances 0.000 claims description 9
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
• UIYJTSIWKMRIEF-UHFFFAOYSA-N 7-methyl-3-[[4-[2-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(C)=CC=C1C1=NN=NN1 UIYJTSIWKMRIEF-UHFFFAOYSA-N 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
• 238000006722 reduction reaction Methods 0.000 claims description 6
• BNGSXGHVQZHPPV-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 BNGSXGHVQZHPPV-UHFFFAOYSA-N 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• CEGGCVVNQNGFPT-UHFFFAOYSA-N 3-[[4-[4-bromo-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-butyl-7-methylimidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Br)C=C1C1=NN=NN1 CEGGCVVNQNGFPT-UHFFFAOYSA-N 0.000 claims description 4
• 206010019280 Heart failures Diseases 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• SUCACHBVGZPQIJ-UHFFFAOYSA-N 2-butyl-3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methylimidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 SUCACHBVGZPQIJ-UHFFFAOYSA-N 0.000 claims description 3
• OVTJRLDKIRWQRH-UHFFFAOYSA-N 2-ethyl-3-[[4-[1-ethyl-3-(2h-tetrazol-5-yl)pyrrol-2-yl]phenyl]methyl]-5,7-dimethylimidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C(N(C=C1)CC)=C1C1=NN=NN1 OVTJRLDKIRWQRH-UHFFFAOYSA-N 0.000 claims description 3
• RJFKLCPHPHROKU-UHFFFAOYSA-N 3-[[4-[2-bromo-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-butyl-7-methylimidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(Br)=CC=C1C1=NN=NN1 RJFKLCPHPHROKU-UHFFFAOYSA-N 0.000 claims description 3
• PWJMOOCJXTXGQF-UHFFFAOYSA-N 3-[[4-[4-bromo-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Br)C=C1C1=NN=NN1 PWJMOOCJXTXGQF-UHFFFAOYSA-N 0.000 claims description 3
• NQAOQSVAXWRKDL-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-5,7-dimethyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C=1N=NNN=1 NQAOQSVAXWRKDL-UHFFFAOYSA-N 0.000 claims description 3
• ABHIOFVVJQEBHY-UHFFFAOYSA-N 7-methyl-3-[[4-[4-methyl-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(C)C=C1C1=NN=NN1 ABHIOFVVJQEBHY-UHFFFAOYSA-N 0.000 claims description 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• GMVKOARZIHFHES-UHFFFAOYSA-N 2-ethyl-5,7-dimethyl-3-[[4-[2-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C(C)=CC=C1C1=NN=NN1 GMVKOARZIHFHES-UHFFFAOYSA-N 0.000 claims description 2
• JYWTUQYDJWROBU-UHFFFAOYSA-N 3-[[4-[1-ethyl-3-(2h-tetrazol-5-yl)pyrrol-2-yl]phenyl]methyl]-5,7-dimethyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C(N(C=C1)CC)=C1C1=NN=NN1 JYWTUQYDJWROBU-UHFFFAOYSA-N 0.000 claims description 2
• AUBCPJWAFNWFQY-UHFFFAOYSA-N 3-[[4-[2,3-dimethyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(C)=C(C)C=C1C=1N=NNN=1 AUBCPJWAFNWFQY-UHFFFAOYSA-N 0.000 claims description 2
• IJZDRCUFOIPZGG-UHFFFAOYSA-N 3-[[4-[2-chloro-3-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(Cl)=C(C)C=C1C1=NN=NN1 IJZDRCUFOIPZGG-UHFFFAOYSA-N 0.000 claims description 2
• LGJSDDZLHLMUSU-UHFFFAOYSA-N 3-[[4-[3-chloro-2-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(C)=C(Cl)C=C1C1=NN=NN1 LGJSDDZLHLMUSU-UHFFFAOYSA-N 0.000 claims description 2
• BVJDHGHXBOUCST-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-ethyl-7-methylimidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 BVJDHGHXBOUCST-UHFFFAOYSA-N 0.000 claims description 2
• NHCJLRILXRWTPK-UHFFFAOYSA-N 3-[[4-[5-bromo-1-ethyl-3-(2h-tetrazol-5-yl)pyrrol-2-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C(N(C(Br)=C1)CC)=C1C1=NN=NN1 NHCJLRILXRWTPK-UHFFFAOYSA-N 0.000 claims description 2
• WERCGTGECUZPKN-UHFFFAOYSA-N 5,7-dimethyl-3-[[4-[2-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C(C)=CC=C1C=1N=NNN=1 WERCGTGECUZPKN-UHFFFAOYSA-N 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 231100000252 nontoxic Toxicity 0.000 claims description 2
• 230000003000 nontoxic effect Effects 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 150000003536 tetrazoles Chemical group 0.000 claims description 2
• 230000003042 antagnostic effect Effects 0.000 claims 2
• LKWLQUVYWDPDQY-UHFFFAOYSA-N (2-butyl-7-methylimidazo[4,5-b]pyridin-3-yl)-[4-[3,4-dichloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methanone Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1C(=O)C(C=C1)=CC=C1N1C=C(Cl)C(Cl)=C1C=1N=NNN=1 LKWLQUVYWDPDQY-UHFFFAOYSA-N 0.000 claims 1
• VXDXEWRBWPOTPX-UHFFFAOYSA-N 3-[[4-[2-chloro-1-methyl-4-(2h-tetrazol-5-yl)pyrrol-3-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=C(Cl)N(C)C=C1C1=NN=NN1 VXDXEWRBWPOTPX-UHFFFAOYSA-N 0.000 claims 1
• OSSWQSCMABLHNH-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 OSSWQSCMABLHNH-UHFFFAOYSA-N 0.000 claims 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
• 125000005236 alkanoylamino group Chemical group 0.000 claims 1
• 150000003840 hydrochlorides Chemical class 0.000 claims 1
• 239000011734 sodium Substances 0.000 claims 1
• 229910052708 sodium Inorganic materials 0.000 claims 1
• 229930192474 thiophene Natural products 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 abstract description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 555
• 238000005481 NMR spectroscopy Methods 0.000 description 444
• 239000000203 mixture Substances 0.000 description 157
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 114
• 239000000243 solution Substances 0.000 description 107
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• 239000003921 oil Substances 0.000 description 28
• 235000019198 oils Nutrition 0.000 description 28
• 239000012044 organic layer Substances 0.000 description 28
• 239000000741 silica gel Substances 0.000 description 28
• 229910002027 silica gel Inorganic materials 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• 239000007787 solid Substances 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000002904 solvent Substances 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 239000012299 nitrogen atmosphere Substances 0.000 description 17
• 238000010898 silica gel chromatography Methods 0.000 description 17
• 235000017557 sodium bicarbonate Nutrition 0.000 description 17
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
• 235000019341 magnesium sulphate Nutrition 0.000 description 16
• 239000007864 aqueous solution Substances 0.000 description 15
• 239000003795 chemical substances by application Substances 0.000 description 15
• 238000001816 cooling Methods 0.000 description 15
• 238000003818 flash chromatography Methods 0.000 description 15
• 229920006395 saturated elastomer Polymers 0.000 description 15
• 239000000725 suspension Substances 0.000 description 14
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• 239000003480 eluent Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
• 239000012267 brine Substances 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 159000000000 sodium salts Chemical class 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• 238000005160 1H NMR spectroscopy Methods 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 238000004440 column chromatography Methods 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
• 229950005499 carbon tetrachloride Drugs 0.000 description 8
• 239000013078 crystal Substances 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• 239000012312 sodium hydride Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• 239000002585 base Substances 0.000 description 7
• 238000010438 heat treatment Methods 0.000 description 7
• 239000005457 ice water Substances 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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